Synthesis of novel fluorinated 1,5-benzothiazepine derivatives and their biological evaluation as anticancer and antibacterial agent

Abstract

A series of novel fluorinated 1,5-benzothiazepine derivatives were synthesized, characterized and evaluated for in vitro anticancer and antibacterial activity. The in vitro anticancer activity of the synthesized compounds 4(a-h) was evaluated against four human cancer cell lines namely lung (A549), breast (MCF-7), liver (HEPG2) and prostate (PC-3) cancer. Compounds 4c, 4d, 4g and 4h exhibited good activity with GI50 <10 ?g ml-1 against all four human cancer cell lines which was comparable to standard drug Adriamycin. Additionally, antibacterial activity of synthesized compounds was estimated using resazurin microtiter assay (REMA) and compared with standard drug Ampicillin. Among the synthesized compounds, 4c, 4d, 4g and 4h showed in good antibacterial activity and all the synthesized compounds were found to be more active towards gram negative than gram positive. These promising results obtained from in vitro anticancer and antibacterial activity, inferred that the synthesized compounds are capable of being anticancer as well as antibacterial agent.

Synthesis of the 1,5‐Benzothiazepane Scaffold – Established Methods and New Developments

“…The reaction is most commonly performed in (anhydrous) methanol or ethanol at reflux temperature with the addition of acetic acid [11,12,[33][34][35][36] or hydrochloric acid [37,38] to aid the condensation of the amino group. Bases, such as pyridine [39] and piperidine, [40,41] have also been used.…”